Yesterday went fine…. Until I got the call. She said ‘I see you’ve taken your boobs’. Uh I didn’t know what to say. So my reply turned out to be, ‘what?!?’. She repeated, ‘I SEE you’ve taken your boobs’. ‘What boobs?’, I said.

I’m just like most crossdressers. I’m not gay and I love to wear women’s clothing. And I too started so early I can’t really remember how young I was the first time. I believe the first few times were when my older sister and cousins dressed me up in their cloths. They had me strip naked, then put panties, hose and a dress on me. I remembered I loved the feeling of the clothes. But I played the game of disliking it while carelessly trying to fight them off. They always won, 3 to 1 anyway.

So flash forward 40 odd years and I’m now accepting the fact that I love to wear women’s clothing. I did bring the subject to the front with my SO. Prior to our little talk I had been wearing panties (mine), her slip and a one-piece bathing suit of hers on occasions during sex. I was even able to ask her to get it and put it on me. She always did this with no question so i thought she was pretty cool about it.

One day I had a talk with my neighbour. She said I should not be ashamed or feel embarrassed about my cross-dressing. Her take is “if it feels good then do it”. She also encouraged me to talk to my SO about it. So I did. I’m a bit confused now about it again. She basically said she does not care for it but knows she cannot and does not want to stop me. However, to be fair she said she could take it sometimes but not all the time. So well we never defined ‘sometimes’ but the fact is I love to do it everyday.

I work from home so as soon as she leaves for work I go and change. I always wear a bra and stockings or pantyhose. On top of this I usually wear a dress but I do have a few skirts and tops I like to wear as well. I bought silicon inserts for my bras that I always love to use everyday too.

But when 5pm rolls around I take most of it off and put on ‘regular’ men clothes. At times I will only have on panties and stockings but I do wear a bra under a t-shirt a few times a week as well. She never says anything but I know she knows I’m wearing a bra. She becomes hesitant to touch me where she could come in contact with the bra.

So basically we live in the ‘don’t tell, don’t wanna know’ mode. She tolerates my dressing during sex and will then touch my bras and other garments then. I love it when she traces her fingers around my bra or rubs me on the panties.

This way of living has left me feeling a bit ashamed since she doesn’t really accept it. It plays that bad tape in my head most of us probably have heard many times growing up. Boys don’t wear girls clothes. So I do hide it a lot.

That is one issue.

Another issue has been that I have increasingly wanted to go out in public dressed up in some fashion. There are two sides to this. The reality and the ‘pushing the envelope’. I sometimes like to push the envelope by wearing panties, garter belt, stockings and a bra out in public under my ‘regular’ clothes. I will almost always have a combination of panties, stockings or pantyhose when I go out, whether it’s alone or with my SO. Recently I have added wearing a bra out. I choose times and places that are somewhat safe. I know my SO has figured it out, one night she even asked. I told the truth. She just says I’m weird.

The next part is that when I’m wearing all of it, dress and all I keep getting the feeling I’d like to be out in public dressed this way. The reality is that I know this would never work. For one I have a beard and I’m very hairy everywhere. I don’t want to go in public as a woman exactly. I’d rather just be able to go in public dressed in women’s clothing. I know that society does not accept this, especially where I live. I have too much fear in doing this, so it keeps me in reality.

The problem is that occasionally I’ll chuck it to the wind and push things further than I should. That’s how I ended up wearing a bra under men’s clothing recently. It seems that my feelings of wanting to be dressed are becoming stronger so I take more risks. But I then think it could be a matter of not wanting to have to hide it so much. I feel this bit churning in the background somewhere.

I hate having to hide it but if I were to allow more to see me dressed up I would not want to deal with the negative aspects. Another complication is that I’d rather not have men see me dressed, I always fantasize about being with other women while dressed up. This includes my SO as well as her friends and my female friends. Maybe it’s a sexual thing then, or a mother thing. I actually do like to be with men sexually but that’s all it is, sex. I never feel compelled to be attracted to a man. It’s about feeling good. I only want to be with a man if I’m dressed in some women’s clothing.

Ok I have not written in a long time. For awhile I just didn’t have anything to write. There were no new thoughts. But I have still been dressing up. In fact I have progressed to wearing silicone breasts in my bras now. I have two sets, one is size C the other set is more of size B. I absolutely love wearing them with my bras.

Wearing bras have become a daily routine now. As well as wearing stockings, pantyhose, slips, dresses and all kinds of women’s clothing. Everyday after my wife leaves for work I go downstairs to my office and get dressed for the day. I wear my women’s outfit while I work all day. It feels nice and gives confidence somehow.

However, around 5pm I have to take it all off and hide it away before my wife comes home. Now I don’t actually have to have a secret about this but my wife has told me not to let her see it. She says every once in awhile is okay. The times I do wear some stuff in front of her is when I want to make love to her. She let’s me. Again there is a but. But I have to make sure I don’t always make love to her wearing a bra and panties. She knows about the bras, panties and stockings. Oh and a couple bathing suits. She does not know I have several dresses, skirts and associated blouses. Nor does she know about the fake boobs. I did get ‘caught’ wearing the small ones the other day. She came outside where I was doing something in the yard. It was dark out and I was hunched over a little so I don’t think she actully saw them. I’m also not sure what I would have done or how I’d feel if she did notice. I might have to think about that.

I’ve included some photos of what I’m wearing right now. I’m over at one our rental houses doing some work. I love to wear a bra under a swimsuit as well as stockings. It makes doing this boring work a bit more fun. This isn’t the best looking swimsuit, too bright for my taste but I do like the way it feels, tight and comfortable. Sort of a calming feeling too maybe. I just like it. I may change into my purple swimsuit in a little bit. I want to put on a bra that the size C fake boobs fit in. I will be working here late so I will be ordering a pizza. I keep thinking about wearing one of my dresses when it’s delivered. I’m not sure I really have the nerve for it though. We’ll see. That would give me something to write about!

Okay, I know it’s been a long time since I posted. Well I suppose at first it was because I really had nothing on my mind that needed to come out. Then there were trickles of thoughts about posting, but thinking that no one really reads this I was discouraged. I have sent various emails, anonymously, to females I have known or known. I always think later that was a really bad bad idea. But then I go do it again.

Last time I wrote to a woman I thought was really beautiful, she’s a friend of an old girlfriend. I have no contact with this person anymore, only have her email address, nothing else. So I emailed her and asked her what she thought about men crossdressing. I didn’t quite put it that way but asked for her opinion on the subject more or less. Then well… I signed my real name.

Geeze, I couldn’t believe I did that. I also did not give her the link to my blog. That might be the only good thing about that. So far I have not heard from her or my old girlfriend whom I do speak with occasionally still.

It’s been several days since I last posted. Lots of things going on lately, mostly with my job. Sometimes I wish I could retire but I’m not quite there yet.

The other day the thought of why I like to crossdress came whizzing by. I have been trying to read some other blogs about other crossdressers. What I found was not what I expected. A large majority of them were not really about crossdressing, they just tagged their blog with it I guess, to attract more visitors. Don’t know really. But I did find real blogs about other crossdressers.

One blog in particular caught my attention the most. He has a nice blog and has been writing for a long time. He has a wife who participates and approves as well. He went on to explain how dressing as a woman was relaxing for him, a way to escape his normal ‘male world’. When dressing as a woman he said he was able to leave all the concerns with his male persona.

This thought about relaxing rang a bell for me. I thought, ‘hum… ya actually it is relaxing to wear lingerie’. I believe I briefly mentioned before how I like the feeling the lingerie gives me of being squeezed in a way. Like someone is holding me almost, a woman.

What grabbed my attention is that he stated he just enjoyed being dressed up as a woman and becoming a woman briefly. That does not happen to me. I feel sometimes more masculine. I’m not trying to be a woman or look like a woman. I am just a man who likes lingerie. I believe the reason for feeling more masculine is that I become more masculine because I have on women’s lingerie. Not that I’m trying to counteract the wearing of it but maybe because I’m more aware of myself. Then could it also be from guilt or shame? I don’t feel that as much now but maybe that plays in there too.

There is this another part point the blogger addressed that interested me. He said for him he derives no sexual pleasure from wearing women’s clothing. That’s different for me. I do get sexual pleasure from wearing women’s clothing. The parts of my body the lingerie is touching tingles and in places more so than others. I like to rub myself from the outside of my panties as well, keeping myself hard for long periods if I can. I especially like being seen by women while wearing just lingerie. That hasn’t really happened since it would upset my girlfriend. Though, I did wear a woman’s swimsuit in front of my girlfriend and her friend when we got in the hottub together.

While writing this I’ve been sitting in just a pair of beige panties I bought today and a beige bra. I’ll have to remove the bra when my girlfriend comes home from work. But later tonight I have to work late again during the night so I’ll have another chance to wear something else.

This past weekend I had to fly out-of-town. The destination and reason are irrelevant. The day I was leaving I had a friend over. I decided to take the opportunity to let her know about my wearing of women’s lingerie. She was surprised as expected. What was nice though was that she made no appearances of negativity towards me or about the idea of me wearing a bra and panties. In fact she made me feel comfortable about it. I was uncomfortable, very embarrassed and feeling a little shame once I let the cat out of the bag. My fear was she would be horrified and tell me off. That was not the case at all. Instead she made a few jokes in my favor about it. I admitted the bra was mine when she asked who’s it was. That was hard to answer but I wanted to tell the truth, so I did. I took her back to our bedroom and showed her some other things. I had some other bras, lots of panties and some slips in a drawer. Of course that was not all of it I explained. The whole time I talked about the lingerie and my desires she kept a smile on her face. That was comforting.

I don’t have a clue why I decided to let her know. I just wanted to. Over te weekend I thought about it a lot. I kept going over that Friday with her. I told my friend ‘it just feels good’ over and over. I think I’m looking for confirmation and acceptance from women I trust so I can accept this burning desire to wear women’s lingerie.

She was so nice about it. She said I should open a business for men who like to wear lingerie. I certainly like that idea but part of this desire is that it’s women’s lingerie. If it were specifically for men it would not feel the same or have the same effect.

Another comment she made that stuck in my head helped me push away some of the shame this weekend. Just before we were to leave for the airport I took my bra off. She said what are you doing that for, why aren’t you going to wear it. Well I have to go through security and I always get the hand wand job. Her comment made me laugh. She said it give him a great story to tell. I still took it off.

However, I decided to put it back on after going through security. In the bathroom stall I retrieved my favorite bra from my bag and put it on. Wow that felt great. I was so glad I put in my bag, it was a quick last-minute decision. I wasn’t going to take any lingerie since I was going to be around family.

That one remark she made about wearing it through security told me it’s okay to feel this way. It meant to me I’m okay too. I’m very glad now I had this conversation with her.

Over the weekend I stole away each night to the hottub at the hotels. I would go down late so no one would be there. I had not come prepared so I had to wear my panties. Now this was a pretty risky move because the only panties I had were the ones I wore on Friday. And they are white. Not only that, they’re slightly see through. To my surprise the panties became almost transparent when wet. At first I was horrified because I saw security cameras at the front desk. Decided the hell with it. I just had to be careful, which I was.

That was exciting. The last night out-of-town. I had a moment alone so I put my bra on and went outside for a smoke. Wearing my fleece pullover helped to conceal it, just in case any family found me.

Now I’m on my way home. I wore my bra and panties to the airport. I had to take It off but could not find a restroom. Well fuckit, I just removed it out in the open near a wall with fewer people around. Once I cleared security I found a restroom so I could put it back on.

I am enjoying the feeling. I can’t exactly explain it. The bra feels good around my chest. It’s not exactly that it squeezes but it’s that I can feel it around me. It gives me a secure feeling.